Biological activities of trans-cinnamaldehyde derived from Cinnamon Bark Oil

Trans-cinnamaldehyde is naturally occurring substance found in cinnamon from the genus of Cinnamomum within Lauraceae family. Cinnamon bark oil extracted contains up to 90% of cinnamaldehyde as main chemical constituent. Its applications are well known as flavor and fragrance material as well as the medicinal purposes. Consequently, numerous experimental results have highlighted cinnamaldehyde as an active chemical constituent in the cinnamon bark oil, contributing significantly to its biological activities.

Some researchers are actively seeking cinnamaldehyde derivatives through modifications of its molecular structure. These derivatives aim not only reduced sensitization and toxic effects, but also for enhanced bioactivities (Doyle and Stephens, 2019). Cinnamaldehyde and its derivatives exhibit bioactivities associated with the cinnamoyl moiety, containing two electrophilic reactive sites in their molecular structures, namely β-carbon on the conjugated double bond and the aldehyde carbonyl group (Figure 1). These sites can react with nucleophilic molecules (Friedman, 2017).

Figure 1. Reactive sites of cinnamaldehyde, i.e. the conjugated double bond (red-dotted cycle) and aldehyde carbonyl group (blue-dotted cycle)

Potential health benefits of cinnamaldehyde have been reviewed by Doyle and Stephens (2019) and Lu et al. (2022). Cinnamaldehyde demonstrates properties as an anti-tumor and anti-cancer agent, particularly for the treatment and prevention of breast cancer (Liu et al., 2020). It also exhibits a cardioprotective function. ameliorating cardiac dysfunction by inhibiting reactive oxygen species (ROS) production (Zhao et al., 2016). Furthermore, it acts as an anti-inflammatory agent (Kim et al., 2018), exerts anti-hyperglycemic and anti-obesity effects through the regulation of endogenous ghrelin release (Camacho et al., 2015; Zhu et al., 2017), and possesses anti-oxidant capabilities (Davaatseren et al., 2017), among other benefits. Additionally, cinnamaldehyde is well-established as an effective inhibitor of insect, mite, tick, mold, bacteria, and yeast growth, as well as microorganism toxin production. The antimicrobial and antibacterial modes of action for cinnamaldehyde have been reported by Shreaz et al. (2016) and Doyle and Stephens (2019).

Bioactivities of cinnamaldehyde

1. Insecticidal

Cinnamaldehyde holds promise as a natural pesticide for controlling plant parasitic nematodes (Lu et al., 2020)

2. Acaricidal

Cinnamaldehyde has a varied toxicity against tick population with the values of LC50 from 0.23 to 2.36 mg/mL (Marchesini et al., 2020)

3. Anti-mold

A combination of cinnamaldehyde and citronellal in specific ratio shows potential as a natural preservative for controlling post-harvest pathogenic molds, including green mold of Penicillium digitatum, and extending the shelf life of citrus fruit (Ouyang et al., 2020)

4. Anti-bacterial

Studies by Suppakul (2016), Doyle and Stephens (2019), and others revealed that antibacterial of cinnamaldehyde has been studied for a number of gram-positive and gram-negative bacteria. The minimum inhibitory concentrations (MICs) of cinnamaldehyde in the range of 0.16-0.63 mg/mL can inhibit the growth of Escherichia coli, Listeria innocua, Salmonella enteritidis, Staphylococcus aureus, Staphylococcus haemolyticus, and Streptococcus sanguinis (Suppakul, 2016)

5. Antifungal

Shreaz et al. (2016) reviewed the cinnamaldehyde as an antifungal agent. Cinnamaldehyde reported to inhibit the fungal growth with the MICs ranging from 0.04 to 0.50 mg/mL for certain yeasts, namely Aspergillus niger, Candida albicans, Coriolus versicolor, Laetiporus sulphureus, and Saccharomyces cerevisiae.

As we continue our exploration of Cinnamon Bark essential oil and cinnamaldehyde, we invite you to connect with us via email at info@ptmitraayu.com or via our contract form here.

References

1. Camacho, S., Michlig, S., Senarclens-Bezencon, C.D., Meylan, J., Meystre, J., Pezzoli, M., Markram, H., and Coutre, J.L. (2015). Anti-obesity and anti-hyperglycemic effects of cinnamaldehyde via altered Ghrelin secretion and functional impact on food intake and gastric emptying. Scientific Reports, 5: 7919.

2. Davaatseren, M., Jo, Y.-J., Hong, G.-P., Hur, H.J., Park, S., and Choi, M.-J. (2017). Studies on the anti-oxidative function of trans-cinnamaldehyde-induced β-cyclodextrin complex. Molecules, 22: 1868.

3. Doyle, A.A. and Stephens, J.C. (2019). A review of cinnamaldehyde and its derivatives as antibacterial agents. Fitoterapia, 139: 104405.

4. Friedman, M., (2017). Chemistry, antimicrobial mechanisms, and antibiotic activities of cinnamaldehyde against pathogenic bacteria in animal feeds and human food. Journal of Agricultural and Food Chemistry, 65: 10406–10423.

5. Liu, Y., An, T., Wan, D., Yu, B., Fan, Y., and Pei, X. (2020). Targets and mechanism used by cinnamaldehyde, the main active ingredient in cinnamon, in the treatment of breast cancer. Frontiers in Pharmacology, 11: 582719.

6. Lu, L., Shu, C., Chen, L., Yang, Y., Ma, S., Zhu, K., and Shi, B. (2020). Insecticidal activity and mechanism of cinnamaldehyde in C. elegans. Fitoterapia, 146: 104687.

7. Lu, L., Xiong, Y., Zhou, J., Wang, G., Mi, B., and Liu, G. (2022). The therapeutic roles of cinnamaldehyde against cardiovascular diseases. Oxidative Medicine and Cellular Longevity, 2022: 9177108.

8. Kim, M.E., Na, J.Y., and Lee, J.S. (2018). Anti-inflammatory effects of trans-cinnamaldehyde on lipopolysaccharide-stimulated macrophage activation via MAPKs pathway regulation. Immunopharmacology and Immunotoxicology, 40: 219–224.

9. Marchesini, P., Novato, T.P., Cardoso, S.J., Prata, M.C.D.A., Nascimento, R.M.D., Klafke, G., Costa-Junior, L.M., Maturano, R., Lopes, W.D.Z., Bittencourt, V.R.E.P., and Monteiro, C. (2020). Acaricidal activity of (E)-cinnamaldehyde and α-bisabolol on populations of Rhipicephalus microplus (Acari: Ixodidae) with different resistance profiles. Veterinary Parasitology, 286: 109226.

10. Ouyang, Q., Okwong, R.O., Chen, Y., and Tao, N. (2020). Synergistic activity of cinnamaldehyde and citronellal against green mold in citrus fruit. Postharvest Biology and Technology, 162: 111095.

11. Shreaz, S., Wani, W.A., Behbehani, J.M., Raja, V., Irshad, M., Karched, M., Ali, I., Siddiqi, W.A., and Hun, L.T. (2016). Cinnamaldehyde and its derivatives, a novel class of antifungal agents. Fitoterapia, 112: 116–131.

12. Suppakul, P. (2016). Chapter 39. Cinnamaldehyde and eugenol: Use in antimicrobial packaging. In Antimicrobial Food Packaging (ed. Barros-Velázquez, J.). Academic Press, p. 479–490.

13. Zhao, H., Zhang, M., Zhou, F., Cao, W., Bi, L., Xie, Y., Yang, Q., and Wang, S. (2016). Cinnamaldehyde ameliorates LPS-induced cardiac dysfunction via TLR4-NOX4 pathway: the regulation of autophagy and ROS production. Journal of Molecular and Cellular Cardiology, 101: 11–24.

14. Zhu, R., Liu, H., Liu, C., Wang, L., Ma, R., Chen, B., Li, L., Niu, J., Fu, M., Zhang, D., and Gao, S. (2017). Cinnamaldehyde in diabetes: A review of pharmacology, pharmacokinetics and safety. Pharmacological Research, 122: 78–89.